Ammonium Chloride → HCID 86709394, compound

HRID 2172252Notes

Reaction equation

HRID 2172252 reaction equation
CC(C)([O-])C.[Na+].Cl[C:8]1[N:9]([CH2:16][CH2:17][CH:18]([OH:44])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]=[C:29]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=4)[S:30][CH:31]=3)=[CH:23][CH:22]=2)[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[N:12]=1.[Cl-].[NH4+]>CC(C)=O>[N+:13]([C:11]1[N:12]=[C:8]2[N:9]([CH:10]=1)[CH2:16][CH2:17][CH:18]([CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]3[N:28]=[C:29]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=4)[S:30][CH:31]=3)=[CH:23][CH:22]=1)[O:44]2)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxide2×HCID 70874643HCID 70874643, compound

Product 1

HCID 86709394HCID 86709394, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium tert-butoxide (62 mg) was added to a dimethyl formaldehyde solution (5 ml) of 4-(2-chloro-4-nitroimidazol-1-yl)-1-{4-[2-(4-trifluoromethoxybenzyl)thiazol-4-yl]phenoxy}butan-2-ol (334 mg), and the mixture was stirred at room temperature. While confirming the progress of the reaction, sodium tert-butoxide (62 mg) was added 3 times, and the resulting mixture was stirred overnight. A saturated ammonium chloride aqueous solution was added to the reaction mixture, and the precipitated solid was sequentially washed with water and diisopropyl ether. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1→ethyl acetate) to afford the title compound as a pale brown powder (69 mg).

Workup

  1. additionwas added 3 times
  2. stirringthe resulting mixture was stirred overnight
  3. washthe precipitated solid was sequentially washed with water and diisopropyl ether
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1→ethyl acetate)

Sources & evidence

ORD record
ord-76c0cfe0e6a94ce7a4d87f58ee2bb1e9
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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